This is a legitimately evolving question. While the community wiki and voting systems partially deal with the problem, there remains the difficulty that at least some of the old answers to questions such as this one are going to lose relevance over time. Is there any policy/user moderation strategy for dealing with this type of situation?

In the case of the above question, the poster was immediately linked to three iterations of essentially the same question, which helps establish the lineage of answers, but at the same time it's going to become frustrating to ask that question over time as legitimately new languages and development frameworks emerge. I have to imagine that there are other questions which behave similarly.

3 Answers
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Close as a duplicate, if possible. That said, if the person asking the question is prudent, they'll already have found the existing questions, and will have phrased their own to separate it from those that came before it (by including sufficient detail about their specific situation). In which case, the question will be answered, and fade into obscurity... until the next imprudent person comes along and asks the exact same thing.

It is my fond hope that this becomes a pattern for asking questions on SO: a very general question can be asked once (or, given the limitations of search and the obstinate refusal of some people to leave duplicates closed, a handful of times), and thereafter closed as a duplicate of the previous instance. More specific questions can be asked, but will fail to attract as wide an audience. Over time, the better general questions will continue to collect viewers and editors to keep them up-to-date, while the specific questions, having fulfilled their purpose, will drop out of sight.

That strategy leads inevitably to an old question with a crop of increasingly irrelevant answers. The primary concern shouldn't be that duplicate questions be prevented when the answer is going to legitimately change over time. There should at least be a strategy for recognizing and providing for the evolution of the question and its answers over time. In the current system there's no decay, so if you perfectly prevent duplicates you put a heavy obstacle in the way of anyone trying to re-evaluate an out-of-date question.
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Mike BurtonSep 4 '09 at 21:30

The alternative to this is the same question asked again and again, with most of the same answers provided again, and again... It's SO: we (the community, in whole or in part) can edit answers. We can alter the search order by voting up new answers and down-voting obsolete ones. We can even dispatch entire questions as "No longer relevant" if necessary, so don't discount the idea that a single question might be kept up-to-date if attention warrants it. And keep in mind: the question you linked to is fundamentally subjective - who alone should decide when an answer is "out of date"?
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Shog9♦Sep 4 '09 at 21:46

I don't like it, because it seems to have a serious problem with historical inertia in the current voting model, but I accept that reasoning.
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Mike BurtonSep 6 '09 at 17:59

The thing here is it takes long enough for this to happen that by the time it's closed there are normally a few answers as well, and so the person who really wants an answer right then can get still one, but we're not leaving the "dupe" sit around active for all eternity. It will point back to the original as long as need be and maybe even eventually be deleted.

Except for potentially offending the question asker everyone is happy. It's the last point we sometimes have a problem with.

In this case, I considered casting a "close-as-duplicate" vote, except for a nagging voice inside my head.

This guy was asking specifically, centered around his current skills (which he enumerated), what he should go after next. Not quite the generalized stuff that preceded, but rather what looked like the best path for him given his specific circumstance. (Note that all the "dupe" links are labeled "similar to." There's a reason, they are similar, but not quite the same to an in-depth reader.)

It can still be argued that it's subjective/argumentative; it can still be argued that it's a dupe, but there was enough there (in its brevity) that I gave the OP the benefit of the doubt and refrained from voting to close.

I found the last "similar to" link (stackoverflow.com/questions/1301908/…) to be extremely similar, with the exception that it specifically requested ideas that might further the learner's career. IMHO, that's close enough, but YMMV. Again, i'd rather let the question author differentiate his question to avoid it being closed, than leave a duplicate open on the off-chance that it might collect some good, fresh, answers (not really seeing much so far... certainly nothing new).
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Shog9♦Sep 4 '09 at 21:53

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Your points on this illustrate, in my mind, why SO simply isn't the place for these questions. But they will come up, time and time again. And either our policy should be close 'em all and let the mods sort 'em out (grin), or evaluate on a case-by-case basis. Personally, I'm torn. Like I said, I gave this OP the benefit of the doubt, but the answers are definitely lacking.
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John RudySep 4 '09 at 21:55